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2-Methyl-2-nitrosopropane
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changed changed 477214185 2-methyl-2-nitrosopropane-2D-skeletal.png correct ?? 100 Skeletal formula of 2-methyl-2-nitrosopropane 2-methyl-2-nitrosopropane-3D-balls.png correct ?? 100 Ball and stick model of 2-methyl-2-nitrosopropane 2-Methyl-2-nitrosopropanetert-nitrosobutane - Compound Summary https://pubchem.ncbi.nlm.nih.gov/compound/23272 PubChem Compound National Center for Biotechnology Information 7 May 2012 USA 26 March 2005 Identification and Related Records tert-Nitrosobutane MNPSingh RJ, Hogg N, Joseph J, Kalyanaraman B Photosensitized decomposition of S-nitrosothiols and 2-methyl-2-nitrosopropane. Possible use for site-directed nitric oxide production FEBS Lett 1995-02-20 360 1 47–51 10.1016/0014-5793(95)00065-h 7875299 https://febs.onlinelibrary.wiley.com/doi/epdf/10.1016/0014-5793(95)00065-H 917-95-3 correct CAS correct FDA JGX6N17V2U 23272 21764 correct chemspider tert-nitrosobutane CC(C)(C)N=O 1S/C4H9NO/c1-4(2,3)5-6/h1-3H3 correct chemspider LUQZKEZPFQRRRK-UHFFFAOYSA-N correct chemspider 4 9 1 1 Blue liquid Ethylamine Ethylenediamine Propylamine Isopropylamine 1,2-Diaminopropane 1,3-Diaminopropane Isobutylamine tert-Butylamine n-Butylamine sec-Butylamine Putrescine
2-Methyl-2-nitrosopropane (MNP or t-nitrosobutane) is the organic compound with the formula (CH3)3CNO. It is a blue liquid that is used in chemical research as a spin trap, i.e. it binds to radicals.
Preparation and structure
Many strong oxidants convert tert-butylamine to the nitroso compound, but none do so in high yield.10.1002/047084289X.rn02280 Encyclopedia of Reagents for Organic Synthesis 2‑methyl-2‑nitrosopropane and 2‑methyl-2‑nitrosopropane dimer Viet D. Nguyen Vu T. Nguyen Oleg V. Larionov 23 Jan 2020 Consequently, t-BuNO is prepared by the following "oscillatory redox" sequence:A. Calder A. R. Forrester S. P. Hepburn 2-Methyl-2-nitrosopropane and Its Dimer 6 803 52 77 cv6p0803
(CH3)3CNH2 → (CH3)3CNO2
(CH3)3CNO2 → (CH3)3CNHOH
(CH3)3CNHOH → (CH3)3CNO
The freshly distilled compound is a blue volatile liquid. Like other nitroso compounds, it features a bent C-N=O linkage. Upon standing at room temperature, the blue liquid converts to the colourless solid that is the dimer (m.p. 74-75 °C). In solution, this dimer quickly reverts to the blue monomer. J. Org. Chem. tert-Alkylnitroso compounds. Synthesis and dimerization equilibriums 3055–3056 36 1971 John C. Stowell 10.1021/jo00819a038 20
Reactions
It can be used as a spin trap. This molecule traps unstable free radicals to form stable paramagnetic nitroxide radicals that can be detected and analyzed by electron spin resonance spectroscopy. It is particularly useful for trapping carbon-centered tyrosyl radicals.J. Biol. Chem.
ESR Spin-trapping of a Protein-derived Tyrosyl Radical from the Reaction of Cytochrome c with Hydrogen Peroxide
15498–15503
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David P. Barr
Michael R. Gunther
Leesa J. Deterding
Kenneth B. Tomer
Ronald P. Mason
http://www.jbc.org/cgi/content/abstract/271/26/15498
10.1074/jbc.271.26.15498
https://web.archive.org/web/20081028161706/http://www.jbc.org/cgi/content/abstract/271/26/15498
2008-10-28
live
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It has also been used in organic chemistry as electrophile to transform sulfones into aldehydes.Rodrigo Eduardo Alonso Inés Cid M. Belén 2018-09-21 A Protocol To Transform Sulfones into Nitrones and Aldehydes Organic Letters 20 18 5789–5793 10.1021/acs.orglett.8b02483 30207472 52186913 1523-7060
MNP is also an efficient regulator of the radical polymerization of methyl methacrylate through the 'pseudoliving' chain mechanism.Dmitry F Grishin Lyudmila L Semyonycheva Elena V Kolyakina 2-Methyl-2-nitrosopropane as a new regulator of the polymer chain growth Mendeleev Communications 1999 9 6 250–251 10.1070/mc1999v009n06ABEH001161
See also
Nitroso
References
Category:Nitroso compounds
Category:Tert-butyl compounds